Casual Vacation Dresses
Jet-setting off to a dreamy destination or planning a spontaneous weekend getaway? Our collection of casual vacation dresses has got your back, ready to make every moment feel like a sun-kissed adventure. Think breezy fabrics, vibrant colors, and effortlessly chic styles that scream "vacay mode activated!" Whether you're strolling through cobblestone streets or lounging by the beach, these dresses are your ultimate travel buddies, keeping you stylishly cool and confidently carefree. So go ahead, pack your bags and slip into something fabulous—your next unforgettable escape awaits!
Home Casual Vacation Dresses
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- Price - High to Low
$38.90
A white sleeveless ribbed knit midi dress with a V-neckline and chic high front slit.
$9.97 $32.90 70% off
An ivory striped ribbed knit mini dress with an off-the-shoulder neckline and long fitted sleeves.
$42.90
A vibrant yellow halter bodycon mini dress in stretchy knit fabric, perfect for any occasion.
$19.97 $49.90 60% off
A lavender skater dress with glitter mesh, sheer sleeves, and a fit and flare silhouette.

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Windsor Mayra Formal Satin Slit Long Dress in Navy Blue-2
$19.97 $59.90
67% off
Slip into the luxe vibes of Mayra! Designed to highlight your figure, this formal satin dress delivers a chic form-hugging fit and a high slit for effortless movement. Fit & FeaturesSmooth satin-knit fabric, moderate stretch, Sleeveless square neckline, spaghetti straps, Fitted bodice, side hip pleating, Form-fitting silhouette, high-cut front slit, Floor-length hem, Style runs small, Where to Wear:Homecoming, weddings, black-tie parties, galas, military balls, engagement parties, rehearsal dinners, bridal celebrations, birthday events, milestone celebrations Free Shipping on All Orders Over $75. | Windsor Mayra Formal Satin Slit Long Dress in Navy Blue-2 | Size: XS | Satin Fabric
Create a captivating entrance in this formal wrap dress for your next soiree. All eyes are on you in this stylishly chic long formal dress with a plunging V-neckline to perfectly display a sparkling rhinestone lariat or delicate layers of dainty necklaces. Fit & FeaturesCrepe fabric, moderate stretch, Asymmetrical wrap V-neckline, Adjustable spaghetti straps, Ruched detailing, slim-fit bodice, High front slit, floor-length wrap silhouette, Runs true to size, Where to Wear:Prom, black-tie weddings, and formal parties. Free Shipping on All Orders Over $75. | Windsor Sasha Formal High Slit Wrap Dress in Black | Size: M | Rhinestone
Chic and glamorous, the Rowena sequin mermaid long dress will stylishly elevate your formal night-out look. With a lace-up strap design and fitted mermaid silhouette with a high slit, you'll deliver stunning style. Fit & FeaturesSheer mesh fabric, knit lining, moderate stretch, embroidered sequin scroll design, Sleeveless square neckline, padded bust, Spaghetti straps, open back, lace-up strap design, tie closure, Lower back zipper with hook and eye closure, High waist seam, Fitted floor-length mermaid silhouette, high front slit, Runs true to size, Where to Wear:Prom, black-tie parties and galas, fancy engagement parties Free Shipping on All Orders Over $75. | Windsor Rowena Sequin Mermaid Dress in Navy Blue | Size: M | Knit Fabric/Mesh Fabric/Sheer Mesh Fabric
Windsor Cheyenne Formal One-Shoulder Velvet Dress in Black
$19.97 $59.90
67% off
Lavish yourself with a luxe formal dress that elevates your special occasion outfit! Cheyenne features a one-shoulder neckline, a wired V-neck bust, a fitted long sleeve, a high side slit on the floor-length hem, and a curve-hugging A-line silhouette. The long dress is composed of a lined velvet fabric that offers a moderate stretch. Complete the look with rhinestone heels and a sphere clutch. Fit & FeaturesOne-shoulder neckline, wired V-neck bust, Fitted long sleeve, High side slit, floor-length hem, A-line silhouette, Lined velvet fabric, Form-hugging fit, moderate stretch, Strapless or sticky bra recommended, Runs true to size, Free Shipping on All Orders Over $75. | Windsor Cheyenne Formal One-Shoulder Velvet Dress in Black | Size: S | Rhinestone/Velvet Fabric
Embellished with light-catching sequins, the Bethanie formal dress is a clear stunner with a lace-up back and a flattering mermaid silhouette with a floor-length hem. Fit & FeaturesSequin-scroll pattern, mesh fabric, stretch knit lining, Sleeveless V-neckline, padded bust, Lace-up back, zipper and hook-eye closure, Mermaid silhouette, Floor-length hem, Runs true to size, Where to Wear:Formal dances, black-tie events, formal weddings, and upscale parties. Free Shipping on All Orders Over $75. | Windsor Bethanie Formal Sequin V-Neck Mermaid Dress in Pink-2 | Size: XXS | Knit Fabric/Mesh Fabric/Mesh Fabric
Designed to be eyed up and down, the Shayla long formal dress brings the sultry heat to any black-tie occasion! A curved neckline and sheer mesh lace corset bodice create a sophisticated silhouette, while the lace-up back provides a personalized fit. Fit & FeaturesSheer mesh, smooth knit fabric, Lace corset bodice, flexible boning, padded bra cups, Lace-up, back zipper with hook-eye closure, Floor-length fitted silhouette, high front wrap slit, Runs true to size, Where to Wear:Formal dances, black-tie galas, red-carpet occasions, and big birthday events, weddings, bridal showers, engagement parties, rehearsal dinners. Free Shipping on All Orders Over $75. | Windsor Shayla Strapless Corset Lace Formal Dress in Red | Size: S | Knit Fabric/Sheer Mesh Fabric
Look your best for a fancy night in the stunning Amirah formal glitter dress! Fashioned with an eye-catching cross back, this dress will make you feel like the star of the evening with a high slit and floor-length column silhouette. Fit & FeaturesGlitter knit fabric, moderate stretch, Sleeveless cowl neckline, Spaghetti straps, cross back, Side pleated seam, slim silhouette, high front slit, Floor-length column silhouette, Runs true to size, Extra glitter for maximum sparkle - may have some natural fallout, Where to Wear:Prom, black-tie weddings, galas, and upscale birthday events. Free Shipping on All Orders Over $75. | Windsor Amirah Formal Glitter Cowl Neck Column Dress in Green | Size: XS | Knit Fabric
Dare to stun in the Jamie satin formal dress crafted with silky satin fabric for a gorgeous sheen. The bold plunge halter neckline and open lace-up back will turn heads while the fitted column silhouette flaunts your curves. Fit & FeaturesSilky satin fabric, short knit stretchy lining, Plunge halter V-neckline, shoulder straps, padded bra cups, Lace-up open back, lower zipper with hook-eye closure, High side slit, Fitted column silhouette, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, galas, and black-tie soirees. Free Shipping on All Orders Over $75. | Windsor Jamie Lace-Up Satin Formal Column Dress in Red | Size: XS | Knit Fabric/Satin Fabric
The Rose formal long column dress is the perfect combination of elegance and glamour with a sheer corset trim and high-side slit for effortless allure! Fit & FeaturesMesh fabric, partial stretchy knit lining, Sleeveless sweetheart neckline, cowl pleating, Adjustable spaghetti straps, crisscross open back, Padded bust, sheer corset bodice, flexible boning, Side ruched seams, fitted column silhouette, High-side slit, floor-length hem, Style runs small, Where to Wear:Prom, weddings, bridesmaids, rehearsal dinners, cocktail soirees, and dressed-up date nights. Free Shipping on All Orders Over $75. | Windsor Rose Formal Mesh Corset Column Dress in Brown | Size: XS | Knit Fabric/Mesh Fabric
Stunning for brides and celebrations, the Savannah formal crepe dress showcases simplicity and chicness! With a form-hugging silhouette and sultry high front slit, this formal dress is perfect for an evening of elegance. Fit & FeaturesLined crepe fabric, moderate stretch, Sleeveless square neckline, tank-style straps, Back zipper and hook-eye closure, Form-hugging silhouette, Front high-cut slit, Floor-length hem, Runs true to size, Where to Wear:Prom, weddings, bridesmaids, red-carpet events, milestone celebrations Free Shipping on All Orders Over $75. | Windsor Savannah Formal Crepe Long Dress in Black | Size: XS
Casual Vacation Dresses
When it comes to packing for a getaway, there’s a special kind of thrill in curating your lineup of casual vacation dresses—the ones that instantly signal “out of office” and let you lean all the way into vacation mode. Whether your spring plans include a sun-soaked escape to the coast, a city break with endless cobblestone strolls, or a spontaneous road trip where the playlist is as important as the destination, your dress game deserves to be as effortless as your itinerary. These are the pieces designed for breezy mornings spent wandering local markets, afternoons chasing sunsets, and those golden-hour dinners where the dress code is equal parts comfort and “I just threw this on” polish. The beauty of windsor vacation dresses is their versatility: think lightweight fabrics that breathe when the temperature spikes, silhouettes that move with you (never against you), and details that make even a simple slip dress feel special—like a smocked bodice, a flirty ruffle, or a tie-back that guarantees a perfect fit after that extra gelato. And don’t underestimate the power of a great dress to turn packing into a breeze; one piece, endless possibilities, zero overthinking.
If you’re shopping for yourself, the right casual vacation dress is a secret weapon—an instant mood-lifter, a space-saver in your suitcase, and a shortcut to feeling photo-ready with minimal effort. If you’re playing the role of gift-giver, these dresses are a thoughtful pick for birthdays, graduations, or even a “just because” treat for the friend who’s always dreaming of her next adventure. Picture her unwrapping a dress that’s ready for her next beach getaway or city escape—suddenly, you’re not just giving her something to wear, you’re giving her a ticket to new memories (and, let’s be honest, some seriously cute photos). Windsor vacation outfits are made for those moments when you want to look put together without sacrificing comfort—perfect for travel days that start with an early flight and end with cocktails by the pool, or for packing light when you’d rather save suitcase space for souvenirs. With March in full swing and spring break on the horizon, there’s no better time to refresh your rotation with styles that work for every itinerary: think midi dresses that go from sightseeing to dinner with a change of shoes, airy maxis that double as swim cover-ups, or playful minis that make every day feel like a celebration.
Shopping for vacation dresses is all about anticipating how you want to feel—relaxed, confident, and ready for whatever the day (or night) brings. Look for easy-care fabrics that won’t wrinkle at the bottom of your bag, adjustable straps for a custom fit, and pockets (because who doesn’t love a dress with pockets?). Don’t shy away from color or print—vacation is the perfect excuse to try something bold, whether that’s a tropical floral, a breezy pastel, or a punchy stripe that pops in every photo. And if you’re someone who loves a little variety, mix it up with a few different lengths and necklines so you’re covered for every occasion, from casual brunches to impromptu dance parties under the stars. For more inspiration and to see the full collection of vacation-ready styles, visit Women's Vacation Dresses. Your next favorite dress is waiting to make every getaway feel like the main event—no stress, just style that travels as well as you do.









